Global Patent Index - EP 0714903 A1

EP 0714903 A1 19960605 - New carbohydrate conjugates as cell adhesion inhibitors

Title (en)

New carbohydrate conjugates as cell adhesion inhibitors

Title (de)

Neue Kohlenhydratkonjugate als Inhibitoren der Zelladhäsion

Title (fr)

Nouveaux carbohydrat conjugués utilisés comme inhibiteurs d'adhésion cellulaire

Publication

EP 0714903 A1 19960605 (DE)

Application

EP 95115588 A 19951004

Priority

DE 4436164 A 19941010

Abstract (en)

[origin: DE4436164A1] Tetrasaccharide conjugates of formula Z-Y-(CH2)n-NH(CO)p-R2 (I) are new. Z = branched tetrasaccharide; Y = O, p = 1 and n = 2-10; or Y = NH(CO), p = 0 or 1 and n = 0-10, provided n and p are not both 0; R2 = amino acid, di- to hexa- peptide, aliphatic or cycloaliphatic lipophilic gp., mixed aliphatic-heterocyclic gp., or triphenylmethane dye. Pref. Z = sialyl Lewis-X or sialyl Lewis-A. R2 = CH2NHCOCH2NH2, CH(S)-CH3NHCOCH(S)-CH2COOHNHCO-CH2NHCOCH(S)-(CH2)3NH(C=NH)NH2NH2, (CH2)6NH2, CH(NH2)-(CH2)2-COOH, CH(NHZ)CH2OBn; Z = benzyloxy; Bn = benzyl; m = 0-10, p, q = 0 or 1; and p or q = 0 when m = 0.

Abstract (de)

Die Erfindung betrifft neue Konjugate von Tetrasacchariden, vorzugsweise von Sialyl Lewis-X (SLeX) und Sialyl Lewis-A (SLeA), mit verbesserter Wirkung als Inhibitoren der Zelladhäsion, ein Verfahren zur Herstellung dieser Verbindungen sowie deren Verwendung als pharmakologische Wirkstoffe und als Diagnostika und Arzneimittel, welche diese Konjugate enthalten.

IPC 1-7

C07H 13/04; C07H 15/04; A61K 31/70

IPC 8 full level

A61K 31/70 (2006.01); A61K 31/7024 (2006.01); A61K 31/7028 (2006.01); A61K 38/00 (2006.01); A61K 39/00 (2006.01); A61K 47/48 (2006.01); A61K 49/00 (2006.01); A61P 9/08 (2006.01); A61P 9/10 (2006.01); A61P 11/00 (2006.01); A61P 29/00 (2006.01); A61P 35/00 (2006.01); A61P 43/00 (2006.01); C07H 3/06 (2006.01); C07H 13/04 (2006.01); C07H 15/04 (2006.01); C07K 5/09 (2006.01); C07K 5/11 (2006.01); C07K 14/78 (2006.01)

CPC (source: EP US)

A61K 47/65 (2017.08 - EP US); A61K 49/0043 (2013.01 - EP US); A61K 49/0052 (2013.01 - EP US); A61P 9/08 (2018.01 - EP); A61P 9/10 (2018.01 - EP); A61P 11/00 (2018.01 - EP); A61P 29/00 (2018.01 - EP); A61P 35/00 (2018.01 - EP); A61P 43/00 (2018.01 - EP); C07H 3/06 (2013.01 - EP US); C07H 13/04 (2013.01 - EP US); C07H 15/04 (2013.01 - EP US)

Citation (search report)

  • [DX] EP 0601417 A2 19940615 - HOECHST AG [DE]
  • [DY] WO 9400477 A1 19940106 - GLYCOMED INC [US]
  • [DY] WO 9202527 A1 19920220 - GLYCOMED INC [US]
  • [DY] WO 9324506 A1 19931209 - ALBERTA RES COUNCIL [CA], et al
  • [Y] EP 0606925 A2 19940720 - GENZYME CORP [US], et al
  • [DY] HASEGAWA ET AL: "synthetic studies on sialoglycoconjugates 52:", J. CARBOHYD. CHEM., vol. 12, no. 8, pages 1203 - 1216, XP000566815
  • [Y] LEE R T ET AL: "Binding characteristics of galactoside-binding lectin (galaptin) from human spleen", J. BIOL. CHEM. VOL.265 (14); PP.7864-71, vol. 265, no. 14, (US), pages 7864 - 7871, XP000566448
  • [Y] OHBAYASHI: "Production of Monoclonal antibodies against Oligosaccharides coupled to Protein", CARBOHYDRATE RESEARCH, vol. 236, AMSTERDAM, NL, pages 349 - 356, XP026610351, DOI: doi:10.1016/0008-6215(92)85030-4
  • [DY] VON DEM BRUCH: "Synthesis of N-Glycopeptide Clusters.....", ANGEW. CHEM. (INT. ED.), vol. 33, no. 1, WEINHEIN,DE, pages 101 - 102
  • [Y] RIO S ET AL: "Synthesis of glycopeptides from the carbohydrate-protein linkage region of proteoglycans", CARBOHYDR. RES., vol. 219, UNIV. ORLEANS;FAC. SCI.; ORLEANS; F-45067; FR. (FR), pages 71 - 90
  • [DPY] W. STAHL ET AL: "Synthesis of deoxy Sialyl Lewisx Analogues, Potential Selectin Antagonists", ANGEW. CHEM., vol. 33, no. 20, WEINHEIM,DE, pages 2096 - 2098

Designated contracting state (EPC)

AT BE CH DE DK ES FR GB GR IE IT LI LU NL PT SE

DOCDB simple family (publication)

US 5858994 A 19990112; AT E217630 T1 20020615; CA 2160100 A1 19960411; DE 4436164 A1 19960411; DE 59510206 D1 20020620; EP 0714903 A1 19960605; EP 0714903 B1 20020515; JP H08325286 A 19961210

DOCDB simple family (application)

US 50907995 A 19950731; AT 95115588 T 19951004; CA 2160100 A 19951006; DE 4436164 A 19941010; DE 59510206 T 19951004; EP 95115588 A 19951004; JP 26176395 A 19951009